1. Field of the Invention
The present invention relates to a novel acid halide derivative and its production, and the production of indanonecarboxylic acid ester using the acid halide derivative as a precursor. Such indanonecarboxylic acid esters are useful as intermediates for insecticides.
2. Description of the Related Art
Indanonecarboxylic acid esters are useful as intermediates for insecticides, and certain processes for producing the same have been known. For example, PCT International Publication No. WO 00/10963 discloses a process for producing an indanonecarboxylic acid ester, in which a halogenated anthranilic acid derivative is allowed to react with sodium nitrite or methyl nitrite to yield a diazonium salt, the diazonium salt is allowed to react with an acrylic acid derivative in the presence of a palladium-containing catalyst to yield a substituted cinnamic acid and an cinnamic ester, the substituted cinnamic acid and cinnamic ester are hydrogenated in the presence of a hydrogenation catalyst to yield a substituted arylpropionic acid, followed by cyclization (ring-closing) in the presence of a base to yield the target compound. However, this process requires the use of a diazonium salt which is difficult to handle in view of safety, inviting problems in production on an industrial scale.
PCT International Publication No. WO 95/29171 discloses a process for producing a substituted indanonecarboxylic acid ester, in which a para-substituted phenylacetyl halide and ethylene are subjected to Friedel-Crafts reaction to yield a substituted tetralone, the substituted tetralone is subjected to ring-opening reaction in the presence of a peroxycarboxylic acid to yield a substituted arylpropionic acid, the substituted arylpropionic acid is esterified, and the ester is subjected to cyclization (ring-closing) reaction in the presence of a base to yield the target compound. This process requires a peroxide for ring-opening of the substituted tetralone and invites problems in safety in production on an industrial scale.
Japanese Unexamined Patent Application Publication No. 05-25164 discloses a process for producing an indanonecarboxylic acid ester by esterifying a substituted indanone with, for example, dimethyl carbonate. As an example, a process for producing methyl indanonecarboxylate is disclosed, in which 5-chloroindanone is allowed to react with dimethyl carbonate in the presence of sodium hydride. However, this process achieves a yield of at most 50% and requires the use of sodium hydride which is dangerous and is difficult to handle.
Certain processes for producing malonic acid diester derivatives, malonic acid monoester derivatives, and acid halide derivatives have been known. For example, J. Med. Chem., 13, 1970, 820 discloses a process for producing diethyl 3-chlorobenzylmalonate by allowing diethyl malonate to react with m-chlorobenzyl chloride in the presence of sodium hydride. J. Amer. Chem. Soc., 74, 1952, 5897 discloses a process for producing a malonic monoester (half ester) by allowing diethyl phenylmalonate to react in the presence of potassium hydroxide in an aqueous ethanol solution. Chem. Pharm. Bull., 22, 1974, 1795 discloses a process for producing ethyl 2-chloroformyl-3-phenyl-propionate by allowing 3-phenyl-2-ethoxycarbonylpropionic acid to react with thionyl chloride. However, these processes have never been applied to the production of a 2-haloformyl-3-phenyl-propionic acid ester having a substituent on its aryl group.